#------------------------------------------------------------------------------ #$Date: 2019-11-08 06:19:29 +0200 (Fri, 08 Nov 2019) $ #$Revision: 225388 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/05/90/7059027.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7059027 loop_ _publ_author_name 'Li, Shasha' 'Xu, Lei' 'Jiang, Liping' 'Zhang, Guofang' 'Zhang, Wei-Qiang' 'Gao, Ziwei' _publ_section_title ; Activation reactions of 2-pyridyl and 2-pyrimidinyl alkynes with Ru3(CO)12 ; _journal_name_full 'New Journal of Chemistry' _journal_paper_doi 10.1039/C9NJ04958D _journal_year 2019 _chemical_formula_sum 'C24.5 H17 Br Cl2 N2 O8 Ru3' _chemical_formula_weight 921.42 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2019-10-30 deposited with the CCDC. 2019-11-07 downloaded from the CCDC. ; _cell_angle_alpha 79.718(6) _cell_angle_beta 86.238(6) _cell_angle_gamma 86.842(6) _cell_formula_units_Z 2 _cell_length_a 7.6301(14) _cell_length_b 10.238(2) _cell_length_c 19.359(4) _cell_measurement_reflns_used 12590 _cell_measurement_temperature 153(2) _cell_measurement_theta_max 26.37 _cell_measurement_theta_min 3.18 _cell_volume 1483.3(5) _computing_cell_refinement 'SAINT (Bruker AXS Inc., 2012)' _computing_data_collection 'APEX2 (Bruker AXS Inc., 2012)' _computing_data_reduction 'SAINT (Bruker AXS Inc., 2012)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2014)' _computing_publication_material 'SHELXTL (Sheldrick, 2014)' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXS (Sheldrick, 2014)' _diffrn_ambient_temperature 153(2) _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device_type 'Bruker APEX II CCD' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0241 _diffrn_reflns_av_unetI/netI 0.0265 _diffrn_reflns_Laue_measured_fraction_full 0.994 _diffrn_reflns_Laue_measured_fraction_max 0.994 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 17384 _diffrn_reflns_point_group_measured_fraction_full 0.994 _diffrn_reflns_point_group_measured_fraction_max 0.994 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.998 _diffrn_reflns_theta_min 2.450 _exptl_absorpt_coefficient_mu 3.083 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 2.063 _exptl_crystal_description block _exptl_crystal_F_000 886 _exptl_crystal_size_max 0.150 _exptl_crystal_size_mid 0.130 _exptl_crystal_size_min 0.100 _exptl_transmission_factor_max 0.7454 _exptl_transmission_factor_min 0.6397 _refine_diff_density_max 0.580 _refine_diff_density_min -1.051 _refine_diff_density_rms 0.096 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 393 _refine_ls_number_reflns 5810 _refine_ls_number_restraints 30 _refine_ls_restrained_S_all 1.069 _refine_ls_R_factor_all 0.0260 _refine_ls_R_factor_gt 0.0234 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0279P)^2^+2.0703P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0584 _refine_ls_wR_factor_ref 0.0601 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5378 _reflns_number_total 5810 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9nj04958d2.cif _cod_data_source_block 9c _cod_original_cell_volume 1483.4(5) _cod_original_formula_sum 'C24.50 H17 Br Cl2 N2 O8 Ru3' _cod_database_code 7059027 _shelx_shelxl_version_number 2014/7 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_min 0.655 _shelx_estimated_absorpt_t_max 0.748 _shelx_res_file ; 9c.res created by SHELXL-2014/7 TITL lishasha20181217_2_0m in P-1 CELL 0.71073 7.6301 10.2381 19.3593 79.718 86.238 86.842 ZERR 2.00 0.0014 0.0020 0.0035 0.006 0.006 0.006 LATT 1 SFAC C H N O Br Ru Cl UNIT 49 34 4 16 2 6 4 OMIT -3.00 52.00 L.S. 10 ACTA BOND $h FMAP 2 PLAN 5 size 0.15 0.13 0.10 simu 0.01 c27 c23 c24 c25 c26 dfix 2.70 0.02 c23 c25 c25 c27 dfix 1.50 0.01 c23 c24 c24 c25 c25 c26 c26 c27 TEMP -120.150 WGHT 0.027900 2.070300 FVAR 0.52967 RU1 6 0.033399 0.348340 0.711638 11.00000 0.02742 0.01540 = 0.01700 0.00021 -0.00333 0.00353 RU3 6 0.170668 -0.108775 0.793838 11.00000 0.01807 0.01293 = 0.01469 -0.00270 -0.00153 0.00018 BR1 5 0.294594 0.022543 1.074911 11.00000 0.02616 0.04037 = 0.01465 -0.00538 -0.00453 0.00148 RU2 6 0.235685 0.122198 0.697603 11.00000 0.01636 0.01697 = 0.01189 -0.00164 -0.00124 -0.00011 C18 1 0.438793 0.101091 0.747944 11.00000 0.02342 0.02197 = 0.01591 -0.00326 0.00248 -0.00245 O4 4 0.563890 0.095030 0.778431 11.00000 0.02434 0.04548 = 0.02400 -0.00374 -0.00881 -0.00274 N1 3 0.167799 0.011194 0.873979 11.00000 0.01694 0.01595 = 0.01463 -0.00234 -0.00134 -0.00132 N2 3 0.089438 0.230411 0.894284 11.00000 0.02473 0.01996 = 0.01883 -0.00472 -0.00165 -0.00046 O8 4 0.205491 -0.226862 0.660147 11.00000 0.05132 0.03728 = 0.02906 -0.01975 -0.00389 0.00378 O7 4 0.511787 -0.268991 0.839405 11.00000 0.02788 0.03593 = 0.04873 0.00017 -0.00827 0.00936 C5 1 0.042390 0.166454 0.781272 11.00000 0.01858 0.01795 = 0.01614 -0.00323 -0.00031 0.00243 C1 1 0.102438 0.138013 0.852725 11.00000 0.01495 0.01519 = 0.01529 -0.00173 0.00190 -0.00061 C7 1 -0.063264 0.078033 0.684340 11.00000 0.01359 0.02562 = 0.01683 -0.00447 -0.00137 0.00186 C6 1 0.001374 0.049209 0.755101 11.00000 0.01402 0.01864 = 0.01609 -0.00202 0.00163 -0.00047 C8 1 -0.144934 -0.014715 0.650085 11.00000 0.01877 0.02819 = 0.02520 -0.00778 -0.00426 0.00115 C21 1 0.188941 -0.179691 0.709388 11.00000 0.02571 0.02140 = 0.02668 -0.00440 -0.00338 0.00104 C20 1 0.387323 -0.210679 0.822934 11.00000 0.02792 0.01827 = 0.02246 -0.00305 0.00033 -0.00272 O1 4 0.215617 0.507389 0.806191 11.00000 0.06955 0.02296 = 0.04044 -0.01063 -0.01275 -0.00649 O5 4 0.415020 0.060469 0.561769 11.00000 0.03943 0.09096 = 0.02601 -0.02565 0.00317 0.00949 C2 1 0.224422 -0.022181 0.939264 11.00000 0.01734 0.02039 = 0.01552 0.00018 -0.00031 -0.00285 AFIX 43 H2 2 0.271191 -0.109558 0.955043 11.00000 -1.20000 AFIX 0 O3 4 0.057878 0.572829 0.583642 11.00000 0.09108 0.03228 = 0.03239 0.01317 -0.01889 -0.01012 C11 1 -0.051848 0.236709 0.574779 11.00000 0.02999 0.03361 = 0.01861 0.00062 -0.00576 0.00444 AFIX 43 H11 2 -0.020293 0.320157 0.548173 11.00000 -1.20000 AFIX 0 C4 1 0.146017 0.196288 0.959067 11.00000 0.02763 0.02348 = 0.01843 -0.00862 0.00025 -0.00104 AFIX 43 H4 2 0.138797 0.260405 0.989192 11.00000 -1.20000 AFIX 0 C17 1 0.355418 0.086038 0.613263 11.00000 0.02296 0.03867 = 0.02279 -0.00690 -0.00413 0.00153 C12 1 -0.028607 0.209651 0.648378 11.00000 0.01916 0.02651 = 0.01903 -0.00325 -0.00458 0.00425 C16 1 0.050908 0.490997 0.631638 11.00000 0.04764 0.02109 = 0.02858 -0.00209 -0.00928 -0.00171 C10 1 -0.118877 0.144612 0.541633 11.00000 0.03446 0.04254 = 0.01837 -0.00377 -0.00869 0.00486 AFIX 43 H10 2 -0.130950 0.164379 0.492288 11.00000 -1.20000 AFIX 0 O2 4 -0.346451 0.413447 0.754363 11.00000 0.04011 0.06927 = 0.09560 -0.00790 0.01417 0.01982 C13 1 -0.219491 -0.141261 0.690822 11.00000 0.02926 0.03276 = 0.03562 -0.00815 -0.00741 -0.00855 AFIX 137 H13A 2 -0.334393 -0.153629 0.673667 11.00000 -1.50000 H13B 2 -0.233013 -0.135392 0.740881 11.00000 -1.50000 H13C 2 -0.139437 -0.216862 0.684347 11.00000 -1.50000 AFIX 0 C14 1 0.143860 0.448647 0.773539 11.00000 0.04413 0.01480 = 0.02683 -0.00057 -0.00107 0.00300 C9 1 -0.169991 0.021363 0.579615 11.00000 0.02746 0.03901 = 0.02998 -0.01391 -0.01078 0.00194 AFIX 43 H9 2 -0.223211 -0.038484 0.555940 11.00000 -1.20000 AFIX 0 C15 1 -0.204687 0.390497 0.738220 11.00000 0.04097 0.03003 = 0.04010 -0.00150 -0.00090 0.01138 O6 4 -0.082520 -0.313959 0.868124 11.00000 0.03464 0.02608 = 0.04520 0.00180 0.00438 -0.00979 C3 1 0.214908 0.069964 0.983487 11.00000 0.01746 0.02698 = 0.01389 -0.00239 -0.00104 -0.00346 C19 1 0.014289 -0.236592 0.843490 11.00000 0.02676 0.01858 = 0.02430 -0.00488 -0.00373 0.00311 CL2 7 0.533681 0.317366 0.934692 11.00000 0.07518 0.06054 = 0.14543 -0.00759 -0.00297 -0.02813 C22 1 0.704966 0.423975 0.929503 11.00000 0.04601 0.05012 = 0.06390 0.01558 -0.00558 -0.00469 AFIX 23 H22A 2 0.663586 0.515130 0.908983 11.00000 -1.20000 H22B 2 0.801789 0.396087 0.897956 11.00000 -1.20000 AFIX 0 CL1 7 0.784172 0.424565 1.012450 11.00000 0.08832 0.06692 = 0.06030 -0.00070 -0.01122 0.00220 PART 1 C23 1 0.609381 0.661162 0.579529 10.50000 0.12826 0.07635 = 0.15832 -0.01942 -0.02691 0.00661 AFIX 3 H23A 2 0.636582 0.650123 0.628009 10.50000 -1.50000 H23B 2 0.708241 0.696293 0.550198 10.50000 -1.50000 H23C 2 0.509062 0.721521 0.571399 10.50000 -1.50000 AFIX 0 C24 1 0.568467 0.527779 0.563426 10.50000 0.11267 0.07974 = 0.14604 -0.03116 -0.04631 0.02189 AFIX 3 H24A 2 0.471266 0.492359 0.593686 10.50000 -1.20000 H24B 2 0.668339 0.467399 0.572703 10.50000 -1.20000 AFIX 0 C25 1 0.523502 0.538048 0.488025 10.50000 0.12110 0.07734 = 0.12494 -0.03493 -0.03887 0.01611 AFIX 3 H25A 2 0.625192 0.562485 0.457535 10.50000 -1.20000 H25B 2 0.432194 0.605406 0.476785 10.50000 -1.20000 AFIX 0 C26 1 0.464862 0.405335 0.475384 10.50000 0.12341 0.08015 = 0.13480 -0.02810 -0.05535 0.00663 AFIX 3 H26A 2 0.362152 0.383035 0.505664 10.50000 -1.20000 H26B 2 0.555163 0.338375 0.489014 10.50000 -1.20000 AFIX 0 C27 1 0.428662 0.406500 0.399812 10.50000 0.12349 0.11383 = 0.14961 -0.05088 -0.05828 0.01582 AFIX 3 H27A 2 0.391682 0.319560 0.397032 10.50000 -1.50000 H27B 2 0.335931 0.471200 0.385912 10.50000 -1.50000 H27C 2 0.531332 0.425990 0.369052 10.50000 -1.50000 PART 0 AFIX 0 H1 2 0.248913 0.293217 0.682287 11.00000 0.04275 HKLF 4 REM lishasha20181217_2_0m in P-1 REM R1 = 0.0234 for 5378 Fo > 4sig(Fo) and 0.0260 for all 5810 data REM 393 parameters refined using 30 restraints END WGHT 0.0280 2.0692 REM Highest difference peak 0.580, deepest hole -1.051, 1-sigma level 0.096 Q1 1 0.6384 0.2936 0.9205 11.00000 0.05 0.58 Q2 1 0.4440 0.4646 0.3868 11.00000 0.05 0.51 Q3 1 0.3499 0.4240 0.4811 11.00000 0.05 0.50 Q4 1 0.6385 0.3629 0.9673 11.00000 0.05 0.43 Q5 1 0.5460 0.2968 1.0194 11.00000 0.05 0.37 ; _shelx_res_checksum 94923 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Ru1 Ru 0.03340(3) 0.34834(2) 0.71164(2) 0.02039(6) Uani 1 1 d . . . . . Ru3 Ru 0.17067(3) -0.10877(2) 0.79384(2) 0.01520(6) Uani 1 1 d . . . . . Br1 Br 0.29459(4) 0.02254(3) 1.07491(2) 0.02695(8) Uani 1 1 d . . . . . Ru2 Ru 0.23569(3) 0.12220(2) 0.69760(2) 0.01518(6) Uani 1 1 d . . . . . C18 C 0.4388(4) 0.1011(3) 0.74794(14) 0.0205(6) Uani 1 1 d . . . . . O4 O 0.5639(3) 0.0950(2) 0.77843(11) 0.0312(5) Uani 1 1 d . . . . . N1 N 0.1678(3) 0.0112(2) 0.87398(11) 0.0158(4) Uani 1 1 d . . . . . N2 N 0.0894(3) 0.2304(2) 0.89428(12) 0.0210(5) Uani 1 1 d . . . . . O8 O 0.2055(3) -0.2269(2) 0.66015(12) 0.0376(6) Uani 1 1 d . . . . . O7 O 0.5118(3) -0.2690(2) 0.83941(13) 0.0386(6) Uani 1 1 d . . . . . C5 C 0.0424(3) 0.1665(3) 0.78127(14) 0.0177(5) Uani 1 1 d . . . . . C1 C 0.1024(3) 0.1380(3) 0.85273(13) 0.0154(5) Uani 1 1 d . . . . . C7 C -0.0633(3) 0.0780(3) 0.68434(14) 0.0187(5) Uani 1 1 d . . . . . C6 C 0.0014(3) 0.0492(3) 0.75510(13) 0.0165(5) Uani 1 1 d . . . . . C8 C -0.1449(4) -0.0147(3) 0.65008(15) 0.0236(6) Uani 1 1 d . . . . . C21 C 0.1889(4) -0.1797(3) 0.70939(16) 0.0246(6) Uani 1 1 d . . . . . C20 C 0.3873(4) -0.2107(3) 0.82293(15) 0.0230(6) Uani 1 1 d . . . . . O1 O 0.2156(4) 0.5074(2) 0.80619(13) 0.0431(6) Uani 1 1 d . . . . . O5 O 0.4150(3) 0.0605(3) 0.56177(13) 0.0509(7) Uani 1 1 d . . . . . C2 C 0.2244(3) -0.0222(3) 0.93926(13) 0.0181(5) Uani 1 1 d . . . . . H2 H 0.2712 -0.1096 0.9550 0.022 Uiso 1 1 calc R U . . . O3 O 0.0579(4) 0.5728(3) 0.58364(13) 0.0533(8) Uani 1 1 d . . . . . C11 C -0.0518(4) 0.2367(3) 0.57478(15) 0.0281(6) Uani 1 1 d . . . . . H11 H -0.0203 0.3202 0.5482 0.034 Uiso 1 1 calc R U . . . C4 C 0.1460(4) 0.1963(3) 0.95907(14) 0.0226(6) Uani 1 1 d . . . . . H4 H 0.1388 0.2604 0.9892 0.027 Uiso 1 1 calc R U . . . C17 C 0.3554(4) 0.0860(3) 0.61326(16) 0.0279(6) Uani 1 1 d . . . . . C12 C -0.0286(4) 0.2097(3) 0.64838(15) 0.0217(6) Uani 1 1 d . . . . . C16 C 0.0509(5) 0.4910(3) 0.63164(17) 0.0324(7) Uani 1 1 d . . . . . C10 C -0.1189(4) 0.1446(3) 0.54163(16) 0.0319(7) Uani 1 1 d . . . . . H10 H -0.1309 0.1644 0.4923 0.038 Uiso 1 1 calc R U . . . O2 O -0.3465(4) 0.4134(3) 0.7544(2) 0.0708(10) Uani 1 1 d . . . . . C13 C -0.2195(4) -0.1413(3) 0.69082(18) 0.0318(7) Uani 1 1 d . . . . . H13A H -0.3344 -0.1536 0.6737 0.048 Uiso 1 1 calc R U . . . H13B H -0.2330 -0.1354 0.7409 0.048 Uiso 1 1 calc R U . . . H13C H -0.1394 -0.2169 0.6843 0.048 Uiso 1 1 calc R U . . . C14 C 0.1439(4) 0.4486(3) 0.77354(16) 0.0292(7) Uani 1 1 d . . . . . C9 C -0.1700(4) 0.0214(3) 0.57962(17) 0.0309(7) Uani 1 1 d . . . . . H9 H -0.2232 -0.0385 0.5559 0.037 Uiso 1 1 calc R U . . . C15 C -0.2047(5) 0.3905(3) 0.73822(19) 0.0382(8) Uani 1 1 d . . . . . O6 O -0.0825(3) -0.3140(2) 0.86812(13) 0.0363(5) Uani 1 1 d . . . . . C3 C 0.2149(3) 0.0700(3) 0.98349(14) 0.0195(5) Uani 1 1 d . . . . . C19 C 0.0143(4) -0.2366(3) 0.84349(15) 0.0231(6) Uani 1 1 d . . . . . Cl2 Cl 0.5337(2) 0.31737(15) 0.93469(11) 0.0942(5) Uani 1 1 d . . . . . C22 C 0.7050(6) 0.4240(5) 0.9295(2) 0.0563(11) Uani 1 1 d . . . . . H22A H 0.6636 0.5151 0.9090 0.068 Uiso 1 1 calc R U . . . H22B H 0.8018 0.3961 0.8980 0.068 Uiso 1 1 calc R U . . . Cl1 Cl 0.78417(19) 0.42456(14) 1.01245(7) 0.0730(3) Uani 1 1 d . . . . . C23 C 0.609(3) 0.6612(13) 0.5795(10) 0.121(5) Uani 0.5 1 d D U P A 1 H23A H 0.6366 0.6501 0.6280 0.181 Uiso 0.5 1 d R U P A 1 H23B H 0.7082 0.6963 0.5502 0.181 Uiso 0.5 1 d R U P A 1 H23C H 0.5091 0.7215 0.5714 0.181 Uiso 0.5 1 d R U P A 1 C24 C 0.568(2) 0.5278(12) 0.5634(8) 0.111(4) Uani 0.5 1 d D U P A 1 H24A H 0.4713 0.4924 0.5937 0.133 Uiso 0.5 1 d R U P A 1 H24B H 0.6683 0.4674 0.5727 0.133 Uiso 0.5 1 d R U P A 1 C25 C 0.524(3) 0.5380(11) 0.4880(8) 0.105(4) Uani 0.5 1 d D U P A 1 H25A H 0.6252 0.5625 0.4575 0.126 Uiso 0.5 1 d R U P A 1 H25B H 0.4322 0.6054 0.4768 0.126 Uiso 0.5 1 d R U P A 1 C26 C 0.465(2) 0.4053(12) 0.4754(8) 0.110(4) Uani 0.5 1 d D U P A 1 H26A H 0.3622 0.3830 0.5057 0.132 Uiso 0.5 1 d R U P A 1 H26B H 0.5552 0.3384 0.4890 0.132 Uiso 0.5 1 d R U P A 1 C27 C 0.429(3) 0.4065(18) 0.3998(8) 0.124(5) Uani 0.5 1 d D U P A 1 H27A H 0.3917 0.3196 0.3970 0.186 Uiso 0.5 1 d R U P A 1 H27B H 0.3359 0.4712 0.3859 0.186 Uiso 0.5 1 d R U P A 1 H27C H 0.5313 0.4260 0.3691 0.186 Uiso 0.5 1 d R U P A 1 H1 H 0.249(5) 0.293(4) 0.682(2) 0.043(11) Uiso 1 1 d . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ru1 0.02742(12) 0.01540(11) 0.01700(11) 0.00021(8) -0.00333(9) 0.00353(9) Ru3 0.01807(11) 0.01293(10) 0.01469(11) -0.00270(8) -0.00153(8) 0.00018(8) Br1 0.02616(15) 0.04037(18) 0.01465(13) -0.00538(12) -0.00453(11) 0.00148(13) Ru2 0.01636(11) 0.01697(11) 0.01189(10) -0.00164(8) -0.00124(8) -0.00011(8) C18 0.0234(14) 0.0220(14) 0.0159(13) -0.0033(10) 0.0025(11) -0.0024(11) O4 0.0243(11) 0.0455(14) 0.0240(11) -0.0037(9) -0.0088(9) -0.0027(10) N1 0.0169(10) 0.0160(11) 0.0146(10) -0.0023(8) -0.0013(8) -0.0013(9) N2 0.0247(12) 0.0200(12) 0.0188(11) -0.0047(9) -0.0016(9) -0.0005(10) O8 0.0513(15) 0.0373(13) 0.0291(12) -0.0197(10) -0.0039(10) 0.0038(11) O7 0.0279(12) 0.0359(13) 0.0487(15) 0.0002(11) -0.0083(10) 0.0094(10) C5 0.0186(13) 0.0179(13) 0.0161(12) -0.0032(10) -0.0003(10) 0.0024(10) C1 0.0149(12) 0.0152(12) 0.0153(12) -0.0017(9) 0.0019(9) -0.0006(10) C7 0.0136(12) 0.0256(14) 0.0168(13) -0.0045(11) -0.0014(10) 0.0019(11) C6 0.0140(12) 0.0186(13) 0.0161(12) -0.0020(10) 0.0016(9) -0.0005(10) C8 0.0188(13) 0.0282(15) 0.0252(15) -0.0078(12) -0.0043(11) 0.0012(12) C21 0.0257(15) 0.0214(14) 0.0267(15) -0.0044(12) -0.0034(12) 0.0010(12) C20 0.0279(15) 0.0183(13) 0.0225(14) -0.0031(11) 0.0003(11) -0.0027(12) O1 0.0696(18) 0.0230(12) 0.0404(14) -0.0106(10) -0.0127(13) -0.0065(12) O5 0.0394(14) 0.091(2) 0.0260(13) -0.0257(13) 0.0032(11) 0.0095(14) C2 0.0173(12) 0.0204(13) 0.0155(12) 0.0002(10) -0.0003(10) -0.0028(10) O3 0.091(2) 0.0323(14) 0.0324(14) 0.0132(11) -0.0189(14) -0.0101(14) C11 0.0300(15) 0.0336(17) 0.0186(14) 0.0006(12) -0.0058(12) 0.0044(13) C4 0.0276(14) 0.0235(14) 0.0184(13) -0.0086(11) 0.0002(11) -0.0010(12) C17 0.0230(14) 0.0387(17) 0.0228(15) -0.0069(13) -0.0041(12) 0.0015(13) C12 0.0192(13) 0.0265(14) 0.0190(13) -0.0033(11) -0.0046(10) 0.0042(11) C16 0.0476(19) 0.0211(15) 0.0286(16) -0.0021(13) -0.0093(14) -0.0017(14) C10 0.0345(17) 0.0425(19) 0.0184(14) -0.0038(13) -0.0087(12) 0.0049(14) O2 0.0401(17) 0.069(2) 0.096(3) -0.0079(19) 0.0142(16) 0.0198(15) C13 0.0293(16) 0.0328(17) 0.0356(17) -0.0081(14) -0.0074(13) -0.0086(13) C14 0.0441(18) 0.0148(13) 0.0268(15) -0.0006(12) -0.0011(13) 0.0030(13) C9 0.0275(15) 0.0390(18) 0.0300(16) -0.0139(14) -0.0108(13) 0.0019(13) C15 0.041(2) 0.0300(17) 0.0401(19) -0.0015(14) -0.0009(15) 0.0114(15) O6 0.0346(12) 0.0261(12) 0.0452(14) 0.0018(10) 0.0044(10) -0.0098(10) C3 0.0175(12) 0.0270(14) 0.0139(12) -0.0024(10) -0.0010(10) -0.0035(11) C19 0.0268(15) 0.0186(14) 0.0243(14) -0.0049(11) -0.0037(12) 0.0031(12) Cl2 0.0752(9) 0.0605(8) 0.1454(15) -0.0076(9) -0.0030(9) -0.0281(7) C22 0.046(2) 0.050(2) 0.064(3) 0.016(2) -0.006(2) -0.0047(19) Cl1 0.0883(9) 0.0669(8) 0.0603(7) -0.0007(6) -0.0112(6) 0.0022(7) C23 0.128(10) 0.076(9) 0.158(12) -0.019(8) -0.027(9) 0.007(8) C24 0.113(8) 0.080(8) 0.146(10) -0.031(7) -0.046(7) 0.022(6) C25 0.121(7) 0.077(9) 0.125(10) -0.035(7) -0.039(7) 0.016(7) C26 0.123(8) 0.080(8) 0.135(10) -0.028(7) -0.055(7) 0.007(7) C27 0.123(10) 0.114(11) 0.150(12) -0.051(9) -0.058(9) 0.016(9) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 C15 Ru1 C16 95.43(15) . . C15 Ru1 C14 97.39(15) . . C16 Ru1 C14 93.24(13) . . C15 Ru1 C5 93.91(13) . . C16 Ru1 C5 166.30(12) . . C14 Ru1 C5 95.47(11) . . C15 Ru1 C12 94.93(14) . . C16 Ru1 C12 92.49(12) . . C14 Ru1 C12 165.85(12) . . C5 Ru1 C12 76.73(11) . . C15 Ru1 Ru2 136.82(11) . . C16 Ru1 Ru2 114.84(10) . . C14 Ru1 Ru2 110.09(9) . . C5 Ru1 Ru2 52.03(7) . . C12 Ru1 Ru2 55.80(7) . . C15 Ru1 H1 173.4(13) . . C16 Ru1 H1 86.1(12) . . C14 Ru1 H1 88.9(12) . . C5 Ru1 H1 83.6(12) . . C12 Ru1 H1 78.6(12) . . Ru2 Ru1 H1 37.8(12) . . C21 Ru3 C19 95.65(13) . . C21 Ru3 C20 89.20(12) . . C19 Ru3 C20 95.62(12) . . C21 Ru3 C6 94.47(11) . . C19 Ru3 C6 102.84(11) . . C20 Ru3 C6 160.70(11) . . C21 Ru3 N1 167.15(11) . . C19 Ru3 N1 96.24(10) . . C20 Ru3 N1 94.48(10) . . C6 Ru3 N1 78.13(9) . . C21 Ru3 Ru2 80.44(9) . . C19 Ru3 Ru2 151.26(8) . . C20 Ru3 Ru2 112.68(8) . . C6 Ru3 Ru2 49.71(7) . . N1 Ru3 Ru2 86.79(6) . . C18 Ru2 C17 93.99(12) . . C18 Ru2 C6 115.83(11) . . C17 Ru2 C6 132.90(12) . . C18 Ru2 C5 99.24(11) . . C17 Ru2 C5 166.75(11) . . C6 Ru2 C5 38.64(10) . . C18 Ru2 C12 162.32(11) . . C17 Ru2 C12 97.33(11) . . C6 Ru2 C12 64.83(10) . . C5 Ru2 C12 70.03(10) . . C18 Ru2 C7 152.08(11) . . C17 Ru2 C7 103.95(11) . . C6 Ru2 C7 37.13(9) . . C5 Ru2 C7 63.50(9) . . C12 Ru2 C7 35.16(10) . . C18 Ru2 Ru1 113.98(9) . . C17 Ru2 Ru1 125.90(10) . . C6 Ru2 Ru1 75.81(7) . . C5 Ru2 Ru1 48.41(7) . . C12 Ru2 Ru1 48.36(7) . . C7 Ru2 Ru1 72.23(7) . . C18 Ru2 Ru3 78.49(8) . . C17 Ru2 Ru3 112.17(10) . . C6 Ru2 Ru3 47.72(7) . . C5 Ru2 Ru3 70.11(7) . . C12 Ru2 Ru3 109.37(7) . . C7 Ru2 Ru3 75.01(7) . . Ru1 Ru2 Ru3 118.065(15) . . C18 Ru2 H1 91.2(13) . . C17 Ru2 H1 98.8(13) . . C6 Ru2 H1 115.0(13) . . C5 Ru2 H1 81.8(13) . . C12 Ru2 H1 73.7(13) . . C7 Ru2 H1 106.6(13) . . Ru1 Ru2 H1 39.6(13) . . Ru3 Ru2 H1 147.8(13) . . O4 C18 Ru2 176.5(3) . . C2 N1 C1 118.4(2) . . C2 N1 Ru3 128.39(18) . . C1 N1 Ru3 113.15(16) . . C4 N2 C1 117.8(2) . . C6 C5 C1 113.3(2) . . C6 C5 Ru1 117.80(18) . . C1 C5 Ru1 128.55(19) . . C6 C5 Ru2 68.12(14) . . C1 C5 Ru2 115.93(17) . . Ru1 C5 Ru2 79.56(9) . . N2 C1 N1 123.3(2) . . N2 C1 C5 121.5(2) . . N1 C1 C5 115.2(2) . . C12 C7 C8 121.2(2) . . C12 C7 C6 113.1(2) . . C8 C7 C6 125.6(2) . . C12 C7 Ru2 70.97(15) . . C8 C7 Ru2 133.38(19) . . C6 C7 Ru2 62.18(13) . . C5 C6 C7 113.3(2) . . C5 C6 Ru3 110.08(18) . . C7 C6 Ru3 125.97(19) . . C5 C6 Ru2 73.24(15) . . C7 C6 Ru2 80.68(15) . . Ru3 C6 Ru2 82.57(9) . . C9 C8 C7 117.8(3) . . C9 C8 C13 120.0(3) . . C7 C8 C13 121.9(3) . . O8 C21 Ru3 176.7(3) . . O7 C20 Ru3 179.8(3) . . N1 C2 C3 120.2(2) . . N1 C2 H2 119.9 . . C3 C2 H2 119.9 . . C10 C11 C12 121.2(3) . . C10 C11 H11 119.4 . . C12 C11 H11 119.4 . . N2 C4 C3 121.7(3) . . N2 C4 H4 119.2 . . C3 C4 H4 119.2 . . O5 C17 Ru2 174.6(3) . . C11 C12 C7 116.7(3) . . C11 C12 Ru1 126.6(2) . . C7 C12 Ru1 116.55(19) . . C11 C12 Ru2 123.6(2) . . C7 C12 Ru2 73.87(15) . . Ru1 C12 Ru2 75.84(9) . . O3 C16 Ru1 177.9(3) . . C11 C10 C9 120.9(3) . . C11 C10 H10 119.6 . . C9 C10 H10 119.6 . . C8 C13 H13A 109.5 . . C8 C13 H13B 109.5 . . H13A C13 H13B 109.5 . . C8 C13 H13C 109.5 . . H13A C13 H13C 109.5 . . H13B C13 H13C 109.5 . . O1 C14 Ru1 175.9(3) . . C8 C9 C10 121.6(3) . . C8 C9 H9 119.2 . . C10 C9 H9 119.2 . . O2 C15 Ru1 178.9(4) . . C2 C3 C4 118.6(2) . . C2 C3 Br1 120.0(2) . . C4 C3 Br1 121.4(2) . . O6 C19 Ru3 174.7(3) . . Cl2 C22 Cl1 111.6(2) . . Cl2 C22 H22A 109.3 . . Cl1 C22 H22A 109.3 . . Cl2 C22 H22B 109.3 . . Cl1 C22 H22B 109.3 . . H22A C22 H22B 108.0 . . C27 C23 C24 42.4(15) 2_666 . C27 C23 C26 74.0(13) 2_666 2_666 C24 C23 C26 37.0(7) . 2_666 C27 C23 H23A 70.8 2_666 . C24 C23 H23A 108.6 . . C26 C23 H23A 144.5 2_666 . C27 C23 H23B 142.2 2_666 . C24 C23 H23B 110.1 . . C26 C23 H23B 95.5 2_666 . H23A C23 H23B 109.5 . . C27 C23 H23C 105.4 2_666 . C24 C23 H23C 109.6 . . C26 C23 H23C 84.0 2_666 . H23A C23 H23C 109.5 . . H23B C23 H23C 109.5 . . C26 C24 C27 95.9(13) 2_666 2_666 C26 C24 C25 41.0(10) 2_666 . C27 C24 C25 136.8(14) 2_666 . C26 C24 C23 71.9(12) 2_666 . C27 C24 C23 30.2(14) 2_666 . C25 C24 C23 111.4(10) . . C26 C24 C25 71.3(12) 2_666 2_666 C27 C24 C25 153(2) 2_666 2_666 C25 C24 C25 35.0(11) . 2_666 C23 C24 C25 142.8(13) . 2_666 C26 C24 H24A 114.1 2_666 . C27 C24 H24A 83.3 2_666 . C25 C24 H24A 109.1 . . C23 C24 H24A 109.7 . . C25 C24 H24A 80.6 2_666 . C26 C24 H24B 134.9 2_666 . C27 C24 H24B 105.0 2_666 . C25 C24 H24B 109.6 . . C23 C24 H24B 109.2 . . C25 C24 H24B 100.7 2_666 . H24A C24 H24B 107.8 . . C25 C25 C26 105(3) 2_666 2_666 C25 C25 C24 73.6(15) 2_666 . C26 C25 C24 38.8(10) 2_666 . C25 C25 C26 39.7(12) 2_666 . C26 C25 C26 144.6(16) 2_666 . C24 C25 C26 110.2(10) . . C25 C25 C24 71.4(12) 2_666 2_666 C26 C25 C24 157(2) 2_666 2_666 C24 C25 C24 145.0(11) . 2_666 C26 C25 C24 36.8(7) . 2_666 C25 C25 H25A 137.5 2_666 . C26 C25 H25A 100.5 2_666 . C24 C25 H25A 109.6 . . C26 C25 H25A 108.8 . . C24 C25 H25A 96.3 2_666 . C25 C25 H25B 110.1 2_666 . C26 C25 H25B 78.3 2_666 . C24 C25 H25B 110.2 . . C26 C25 H25B 109.9 . . C24 C25 H25B 82.2 2_666 . H25A C25 H25B 108.1 . . C24 C26 C25 100.2(15) 2_666 2_666 C24 C26 C27 44.8(10) 2_666 . C25 C26 C27 144.9(16) 2_666 . C24 C26 C23 71.1(11) 2_666 2_666 C25 C26 C23 162(2) 2_666 2_666 C27 C26 C23 30.5(10) . 2_666 C24 C26 C25 71.9(12) 2_666 . C25 C26 C25 35.5(16) 2_666 . C27 C26 C25 112.9(11) . . C23 C26 C25 142.5(13) 2_666 . C24 C26 H26A 108.5 2_666 . C25 C26 H26A 78.9 2_666 . C27 C26 H26A 110.9 . . C23 C26 H26A 89.3 2_666 . C25 C26 H26A 107.8 . . C24 C26 H26B 141.6 2_666 . C25 C26 H26B 99.3 2_666 . C27 C26 H26B 108.8 . . C23 C26 H26B 96.7 2_666 . C25 C26 H26B 108.9 . . H26A C26 H26B 107.5 . . C23 C27 C24 107(3) 2_666 2_666 C23 C27 C26 75.5(17) 2_666 . C24 C27 C26 39.4(9) 2_666 . C23 C27 H27A 33.2 2_666 . C24 C27 H27A 140.4 2_666 . C26 C27 H27A 106.9 . . C23 C27 H27B 111.3 2_666 . C24 C27 H27B 76.9 2_666 . C26 C27 H27B 109.7 . . H27A C27 H27B 109.5 . . C23 C27 H27C 132.6 2_666 . C24 C27 H27C 104.4 2_666 . C26 C27 H27C 111.8 . . H27A C27 H27C 109.5 . . H27B C27 H27C 109.5 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 Ru1 C15 1.903(4) . Ru1 C16 1.933(3) . Ru1 C14 1.967(3) . Ru1 C5 2.096(3) . Ru1 C12 2.124(3) . Ru1 Ru2 2.7554(5) . Ru1 H1 1.80(4) . Ru3 C21 1.898(3) . Ru3 C19 1.906(3) . Ru3 C20 1.965(3) . Ru3 C6 2.076(3) . Ru3 N1 2.142(2) . Ru3 Ru2 2.7828(5) . Br1 C3 1.881(3) . Ru2 C18 1.867(3) . Ru2 C17 1.903(3) . Ru2 C6 2.141(3) . Ru2 C5 2.209(3) . Ru2 C12 2.351(3) . Ru2 C7 2.389(3) . Ru2 H1 1.73(4) . C18 O4 1.148(3) . N1 C2 1.342(3) . N1 C1 1.367(3) . N2 C4 1.334(4) . N2 C1 1.343(3) . O8 C21 1.140(4) . O7 C20 1.127(4) . C5 C6 1.440(4) . C5 C1 1.460(4) . C7 C12 1.432(4) . C7 C8 1.440(4) . C7 C6 1.461(4) . C8 C9 1.371(4) . C8 C13 1.511(4) . O1 C14 1.131(4) . O5 C17 1.136(4) . C2 C3 1.379(4) . C2 H2 0.9500 . O3 C16 1.135(4) . C11 C10 1.369(5) . C11 C12 1.423(4) . C11 H11 0.9500 . C4 C3 1.383(4) . C4 H4 0.9500 . C10 C9 1.404(5) . C10 H10 0.9500 . O2 C15 1.130(4) . C13 H13A 0.9800 . C13 H13B 0.9800 . C13 H13C 0.9800 . C9 H9 0.9500 . O6 C19 1.133(4) . Cl2 C22 1.735(5) . C22 Cl1 1.754(5) . C22 H22A 0.9900 . C22 H22B 0.9900 . C23 C27 0.80(2) 2_666 C23 C24 1.507(9) . C23 C26 1.515(19) 2_666 C23 H23A 0.9601 . C23 H23B 0.9600 . C23 H23C 0.9600 . C24 C26 0.959(18) 2_666 C24 C27 1.065(18) 2_666 C24 C25 1.505(9) . C24 C25 1.524(19) 2_666 C24 H24A 0.9600 . C24 H24B 0.9600 . C25 C25 0.91(3) 2_666 C25 C26 1.003(17) 2_666 C25 C26 1.519(9) . C25 C24 1.524(19) 2_666 C25 H25A 0.9600 . C25 H25B 0.9600 . C26 C24 0.959(18) 2_666 C26 C25 1.003(17) 2_666 C26 C27 1.504(9) . C26 C23 1.515(19) 2_666 C26 H26A 0.9600 . C26 H26B 0.9600 . C27 C23 0.80(2) 2_666 C27 C24 1.065(18) 2_666 C27 H27A 0.9600 . C27 H27B 0.9600 . C27 H27C 0.9601 .